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Herein, we report a systematic study of the regiospecific impact of four constitutional isomers of non\u2010natural fluoro\u2010Trp, regarding their incorporation at either\n                    <jats:italic>edge<\/jats:italic>\n                    \u2010 or\n                    <jats:italic>face<\/jats:italic>\n                    \u2010positions. Single fluorine substituents affect the electron density of the indole moiety and introduce a highly electronegative component while the native geometry of Trp is maintained. We employed a library approach based on the sequence of Trpzip2 and assessed peptide structure and stability using CD, FTIR, and NMR spectroscopy. Global hairpin stability was improved or compromised upon site\u2010specific incorporation of a single monofluoro\u2010Trp regioisomer. Fluorine substitution revealed key CH\/\u03c0 interactions within the Trp\/Trp packing and holds potential for the future optimization of aromatic interactions involving Trp.\n                  <\/jats:p>","DOI":"10.1002\/chem.202501263","type":"journal-article","created":{"date-parts":[[2025,6,19]],"date-time":"2025-06-19T10:05:27Z","timestamp":1750327527000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Investigating the Site\u2010Specific Impact of Fluorine Substitution on Aromatic Interactions in a Tryptophan Zipper Peptide"],"prefix":"10.1002","volume":"31","author":[{"ORCID":"https:\/\/orcid.org\/0009-0009-9136-0717","authenticated-orcid":false,"given":"David","family":"Reiter","sequence":"first","affiliation":[{"name":"Institute of Chemistry and Biochemistry Freie Universit\u00e4t Berlin  Arnimallee 20 14195 Berlin 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